


Stiles, Isaac, and Jackson

by distraughtlover



Series: Stiles, You Lucky Bastard [8]
Category: Teen Wolf (TV)
Genre: Bottom Jackson Whittemore, M/M, Plot What Plot/Porn Without Plot, Top Isaac Lahey, Top Stiles Stilinski
Language: English
Status: Completed
Published: 2018-07-13
Updated: 2018-07-13
Packaged: 2019-06-09 22:16:00
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,504
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15277335
Author URL: https://archiveofourown.org/users/distraughtlover/pseuds/distraughtlover
Summary: After a party, Stiles, Isaac, and Jackson have one of their own.





	Stiles, Isaac, and Jackson

Because it was now late April, the preparation for finals had started, the last necessary step before the end of high school towards the path of graduation. It was all becoming a bit scary now, but incredible excitement was building up as well. 

And yet, some things still felt the same, like the fact that it was only Monday and the rest of the week loomed ahead. 

Stiles walked through the halls in one of the school’s buildings, picked up a few items from his worn locker, and felt ready to head home. Then his phone bleeped with a text message. It was from Jackson, asking if he could meet for a moment. Stiles typed ‘sure’ and asked where he was. Once Jackson told him where, Stiles exited the building. 

Stiles found Jackson waiting outside, standing next to a table. As he came up to him, Stiles was distracted by the other boy’s supreme looks and stumbled over his feet and almost crashed into Jackson. As he steadied himself, Stiles was inadvertently leaning over Jackson, his chest exhaling for a couple of moments. Realizing how it looked, Stiles straightened up and moved a couple inches away so he wouldn’t be flush with Jackson, yet still felt a little embarrassed from his stumble. 

Jackson laughed innocently at his mistake and found it completely endearing. 

“That was incredibly cute, Stiles. You know, being a bumbling guy brute is kind of a turn-on for me,” Jackson said. 

Stiles felt his embarrassment dissipate and laughed. 

“You should watch me at Lacrosse practice, then,” Stiles said with a grin. 

They talked for a couple of minutes and then Jackson brought up what he had been wanting to say. 

“So here’s the thing; my parents will be out of town this weekend so I’ll be throwing a party this Friday night, but I’m telling you earlier than everyone else for a couple of reasons,” Jackson said. 

“Lay ‘em on me,” Stiles said. 

“Well, I was hoping you’d be able to…spend the night,” Jackson said, his eyes emitting sensual clarity that sparked something within Stiles.

“Fuck yes I can. All you have to do is bat an eyelash, that’s how fucking whipped I am,” Stiles said, answering immediately. 

They looked at each other, lust already forming. 

“I’m glad you’re that willing already,” Jackson said, smirking.

“For you, I definitely am,” Stiles said. 

Jackson paused for a short couple of seconds, then continued. 

“Here’s the other thing, though,” Jackson began, “what would you say to…including Isaac?” 

Stiles smiled with surprise but was not displeased at hearing his proposition. 

“Just out of curiosity, how come?” Stiles asked.

“Don’t worry, I’m not being greedy. I just think it might be a nice time for all three of us,” Jackson said.

Recalling the fantastic sex he had had with Isaac, Stiles was already sold.

“I’m totally down for it,” Stiles said. 

“Then its settled,” Jackson said smiling. 

The next day Stiles and Isaac talked privately about the impending date of Friday night. 

“Are you as fucking excited as I am?” Stiles asked Isaac in a private corner of their school.

“Dude, fuck yeah. From what you’ve told me, Jackson sounds like the most perfect twink ever,” Isaac said. 

Their anticipation steadily rose until Friday night had arrived and both guys were inside Jacksons house where a full party was occurring. A lot of people had been invited and a fun, unhurried vibe had been steady throughout the time of the party. 

Stiles leant against the kitchen island, talking to a couple guys from the basketball team. He turned his head and noticed Isaac with Scott and Allison at the breakfast table along with a couple of other people, then they became blocked as other students passed by. 

As music rang at a nice but acceptable volume, Stiles alternated between laughing and making people laugh. Everyone was having a good time. 

Close to eleven, the party began to die down until only just a few remained. Stiles and Isaac had made up the excuse of helping Jackson clean up the house in order for them to stay behind (and to be truthful, they would actually help Jackson clean up his house) then said goodbye to the last people who departed the home. 

It was just the three of them now. 

They were on the couch in the living room, Jackson seated in the middle of them. 

“So listen, before we get…started, I’m going to ready myself. Think you guys can wait for a bit?” Jackson asked them.

Isaac slung his arm around Jackson and said jovially, “I’d wait for as long as you needed me to.”

Jackson stood up and faced Isaac and Stiles. 

“It may not take too much time, or it may take a while. But, I hope you both can remain patient with me,” Jackson said. 

They nodded their agreement, completely willing to wait as long they had to. 

Jackson gently smiled then turned to walk away. He paused for a second and looked back at them. 

“Oh, and please don’t get started without me,” Jackson teased breathily. 

Stiles and Isaac watched him walk away with slightly parted mouths, both of them already half-hard and extremely ready to please the muscular yet thin little twink who had been the focus of both their wet dreams more than once. The three of them had ended up revealing earlier how Stiles had slept with both of them already, and that made things even easier. 

It was now just Stiles and Isaac downstairs. 

“Man, I’m fucking pumped, in more ways than one,” Stiles joked. 

“Me too, but I’m so worried I’m not gonna be good enough for him,” Isaac revealed. 

“Don’t even worry about that, you’re going to be fucking fantastic,” Stiles said. 

Jackson reappeared downstairs after forty minutes had passed. The anticipation had not diminished; it grew exponentially. He wore a blank baby blue T-shirt that looked soft to the touch and hung lightly from his upper region. Below him was a pair of dark gray sleeping shorts that rose just a sliver above the knees. 

He was astoundingly beautiful. 

Even though Stiles and Jackson had gone to bed before, this felt different for the former not only because of the inclusion of Isaac, but also since it seemed that Jackson became more and more breathtaking. 

“Are you guys ready to take this upstairs?” Jackson asked. 

They stood up immediately and followed him up the stairs. Stiles did his best not to stare at the beauty in front of him, but Isaac was gaping at his perfect butt, backside, and legs. 

Jackson led the two other guys down the upstairs hall and into his bedroom. Stiles remembered it clearly, the generous size, the comfy king bed, and the sofa next to it. They left the door partially open and took off their shoes. 

The energy between all three was radiating. Jackson turned and faced Stiles, and they both slowly but instinctively leaned forward and kissed softly. Then when they broke off, Jackson swiveled around and Isaac leaned down to kiss him. 

After Stiles and Isaac had kissed, all three of them began to undress. Stiles took off his green and gray plaid shirt, dropping it to the floor, then pulled off his gray T-shirt. Isaac wasted no time and his orange-red T-shirt was gone in a second, flying off his body. After Jackson slipped graciously out of his shirt, they all collided together. Jackson held onto Isaac as they attached their lips again, while Stiles stood behind him and slowly grinded while mouthing at the skin available. 

Isaac began unbuckling his jeans eagerly and they dropped to the ground, Stiles following as well. Jackson let his shorts drop silently and they were now in just their underwear. They all shared hot kisses between each other with hands that traveled over hard muscles and delicate skin. 

Stiles dropped his hands and held them against Jacksons clothed hips.

“Here, let me get these off for you,” he whispered. 

He went down to his knees and faced Jacksons backside. Slowly, he pushed down the underwear until they slid off completely and Jackson was left bare. Stiles gazed at the most perfect ass in front of him, in awe that such a complete beauty existed. 

Then Jackson slipped away and sat on the edge of the bed facing them in his beautiful, subdued glory. 

“Time to impress me,” Jackson said smiling.

Isaac and Stiles came forward until they stood in front of him, then dropped their underwear at the same time. They stood completely bare before Jackson with hard thick cocks that stood straight up. Jackson scooted back up the bed in a smooth motion and invited the two other guys to join him. Isaac and Stiles went on opposite sides of him and kissed hungrily at his neck. 

Then Jackson latched both his hands onto their throbbing cocks and they jerked up into his warm grip. Jackson moaned deliciously as he held two thick manly cocks in his hands and as he was being loved by the two guys. 

“Both of you lay down,” Jackson told them. 

They switched and then Stiles and Isaac were laying against the headboard with Jackson in front of them. Jackson lowered himself down and then opened up his mouth to take in Stiles’ dick while holding onto Isaac’s length. 

“Fuck,” Stiles said drawling out the word.

Jacksons mouth was astounding working its way up and down the length of Stiles’ dick. As Jackson worked, Stiles and Isaac reached out and rubbed each other’s nipples, hardening them up. 

Then Jackson popped his mouth off momentarily. 

“You taste so good,” Jackson said to Stiles. His sweet voice grazed over the words he uttered and Stiles felt himself harden more. 

He dipped back down and sucked Stiles off, feeling chills as his lips grazed gently down Stiles’ stiff dick. After slurping on just the head, Jackson moved down and licked at his nuts while still jerking off Isaac. After inhaling the smell of Stiles’ manly balls, Jackson sucked them off. 

Then it was Isaac’s turn. 

Jackson moved his head over and went to work pleasuring Isaac and his cock. He moaned at the long cock inside his mouth with a large mushroom head and slurped over it. Jackson breathed in the scent of Isaac’s heavy balls, then rolled them gently in his hand. He went in for another whiff, his nose underneath Isaac’s sack, and when he removed his face, said, “Fuck, I absolutely love the smell of men.” 

The three of them then stood up on their knees atop the soft bed. 

As Stiles held onto Jackson, he leant his head down and inhaled the intoxicating vanilla scent coming off Jacksons slender neck. He soon found out the entirety of Jackson’s beautiful body smelled of pure, sweet vanilla. 

Stiles traveled the whole length of Jacksons entirely smooth body and felt himself becoming enamored. The two of them rolled around the bed in their gorgeous nudity until Stiles covered Jacksons body. He began thrusting atop while Jackson held on tightly, and with their bodies so close, Jackson caught the scent of Stiles’ deodorant, cologne, and slight sweat. 

When it was time, Jackson switched over to Isaac. Jackson swirled around Isaacs nipple in his mouth and caressed his strong chest. He moved his head to the side, catching the scent of Isaac’s deodorant and slight sweat, then went up and mouthed at his capable shoulder. Isaac reached his hand down and held Jacksons sweet bubble butt while his other arm was wrapped securely around Jacksons lower back, holding their chests close together. Stiles went behind Jackson and pressed his chest against him. 

The combining of their three bodies created a harmony of comforting warmth and lustful astonishment. 

Then they moved again. Stiles sat against the headboard while Isaac moved to the back of Jackson. 

Jackson stretched out as he remained on his hands and knees. He gripped Stiles’ cock and dropped his head, opening his mouth and filling it up with dick. Isaac went behind him and began caressing his butt, gazing with wonder at the firm, rounded cheeks. He spanked him lightly a couple of times and then moved his head forward. Going slow and easy, Isaac pushed his tongue out and lapped at Jacksons hole, groaning with lust. Isaac was in pure astonishment at the gorgeous, perfect butt that belonged to Jackson. He couldn’t believe he was being granted to such perfection. 

Stiles watched as Jackson created a tight suction with his mouth, traveling up and down his stiff length. His lips parted over the ridge of Stiles’ mushroom head, then sucked it repeatedly, popping his mouth off and then onto it over and over. Stiles became slack-jawed from the incredible feeling, then relaxed back against the pillows and smiled upward as Jackson continuously sucked his entire cock. 

Jackson stayed in the middle as Isaac and Stiles switched their original positions. Isaac hopped up onto the bed and settled himself down. He splayed out his lengthy athletic legs for Jackson to lay between. Meanwhile, Stiles went around and placed himself behind Jacksons butt, doing all he could to please Jackson. He ate out his perfect hole and held onto the perfect ass, still in disbelief that such perfection could exist. 

In the middle, Jackson gently touched Isaac’s warm thighs with his fingers as he enthusiastically sucked the cock in front of his face. Isaac stared open-mouthed at the true beauty in front of him. 

They all felt ready to move on. 

There was a box of condoms on one of the nightstands along with a bottle of lube. After the two guys watched with hooded eyes as Jackson prepped himself, Jackson fished out a condom and flicked it to Isaac. 

“Come on, big boy,” Jackson purred softly to Isaac. 

Isaac quickly bounded over, quaking the bed like the large muscular brute he was, then hurriedly suited up his throbbing cock with an eager smile on his face and lathered it up. Jackson lay back against the pillows, watching him with Stiles by his side. He sensually opened up his legs for Isaac to fit between. Once he was ready, Isaac moved forward and gripped Jacksons thigh, then pointed his dick down to Jacksons entrance. 

Jackson gently bit his bottom lip as he felt Isaac’s cock slowly push through his hole, emitting a lustfully enthralled smile from the immensely pleasurable feeling. 

Once Isaac slid all the way in, Jackson arched up and Isaac groaned. They stayed completely connected for several moments until Isaac began to pull away. When his cock was halfway out, he slid back inside fully. 

“Holy shit,” Isaac expressed. His cock was in heaven from Jacksons gorgeous, tight, and welcoming hole. 

Then, Isaac leaned his large muscular frame over Jackson and began thrusting. Jackson skidded his fingers across Isaac’s sides, then snaked a hand over to his rippling back, eventually traveling down until his palm rested atop Isaac’s ass. With his other hand, Jackson reached out and languidly stroked Stiles’ cock. Stiles bucked up into his grip and shifted closer to him. 

Jackson was the most sensual creature Stiles had ever encountered. 

“Fuck, you were made for taking cock,” Isaac grunted to Jackson. 

As Isaac thrusted, Jackson turned his head and looked up at Stiles. 

“Hey Stiles, do you think you could get my water from the dresser? I need a drink and I’d be really grateful,” Jackson said, throwing forth a beautiful spark from his gorgeous, sensual eyes, emitting such pure sensuality that it knocked Stiles off his inner balance. 

Stiles quickly nodded his head, willing now to do anything for Jackson. But in his haste to please Jackson, Stiles moved off the bed backwards and bumped into the nightstand, accidentally knocking over the lightweight lamp to the carpet. 

“Shit!” Stiles exclaimed. 

The lamp didn’t break; it only needed to be set back up, but Stiles still panicked and hurriedly tried to fix his mess, bumbling around stark naked. He bent over, revealing his toned butt to Jacksons waiting eyes, then straightened up and put the lamp back the way it was, making sure nothing was wrong. 

“Like I told you before, I love when men turn into embarrassed brutes, especially when they’re completely nude,” Jackson said. 

Isaac had hardly noticed anything; he was only focused on making sure Jackson felt pure pleasure. Stiles then walked over to the dresser at the front of the bedroom, his cock waving up and down. He picked up the bottle and went back to Jackson, handing it to him. After Jackson held the bottle and took a small sip, he put the bottle on the nightstand and held onto Stiles’ cock next. 

Isaac let himself slide out of Jackson. It was now Stiles’ turn. 

When Stiles had suited up, Jackson climbed into his lap. He grabbed Stiles’ cock and then began to slide down it, having an ease about it. They both moaned once Jackson was seated. Stiles’ hands fit perfectly across Jacksons beautiful golden ass. He squeezed it with care and massaged him unhurriedly. 

Jackson began lightly riding. Stiles loved how good it felt to have his hole sliding up and down his dick. Then he moaned as Jackson rode faster, getting filled up by every inch of Stiles. 

Experiencing a surge of carnality, Stiles picked Jackson up and moved them forward to the front of the bed. He placed Jackson on his back and thrusted repeatedly, needing to feel the warm tightness of Jacksons hole. 

“Fuck me, Stiles,” Jackson moaned. 

He went quicker, pounding Jacksons hole with passion and intensity. Stiles felt sweat collecting on his forehead, so he swiped the front of his arm across it and continued to pound Jackson. 

On his back, Jackson turned his head and looked at Isaac. 

“Isaac, why don’t you come take a seat on my face?” Jackson said.

Isaac looked at him and then quickly shot up from the bed, not wanting to disappoint Jackson for even a second, and hurriedly walked naked to where his head was. He turned himself around and scooted back towards Jacksons head. Then he took a squatting position, his ass only a few inches above Jackson. 

“Uh uh. I want you covering me,” Jackson said, then grabbed Isaacs thighs and pulled him down. 

Jacksons face became obscured from view by Isaacs herculean ass. The point of his chin and his neck were the only things visible to Stiles. 

Stiles had slowed down his speed considerably so he wouldn’t be shoving Jackson back and forth as fast, and also to avoid busting early. 

With his face covered by Isaac’s ass and balls, Jackson breathed in the rich manly scent, then went to work eating out his asshole. 

“Hell yeah, dig that tongue up there!” Isaac exclaimed. 

With his muscled ass still firmly planted down, Isaac shook his hips, jostling Jacksons head. Stiles watched as Jackson lovingly spanked Isaac’s large butt cheeks and held onto the taut rounded skin.

“Eat that fucking hole!” Isaac said. 

Jackson lightly pushed Isaac’s thighs up. Isaac stood up slightly but still remained in a bent position. Jackson needed a breather for just a few moments. As he did so, he delicately caressed Isaac’s thick brawny thighs and stared upwards at Isaac’s underside. Stiles continued to gingerly thrust into him. Then he was instantly ready to go again. Isaac sat back down completely and Jackson went back to his incomparably pleasurable work of eating out Isaac’s hole and inhaling the delectable smell of Isaac’s burly ass. 

Isaac and Stiles worshipped Jackson and his body. Stiles knew it was because of how much beauty, grace, and sensuality Jackson held. Although, because of these gorgeous qualities, Stiles viewed himself and Isaac as big dumb jocks compared to Jackson. It didn’t really matter, though, because everything Stiles felt since the night had started was incomparable and something he would never forget. 

Stiles pulled out of Jackson. Jackson began turning with ease until his body lay facing forward to Isaac, who was standing tall and naked with his strong chest puffed, most likely wanting to impress Jackson. Jackson lay still atop the soft comforter, gazing at Isaac. As Stiles stood up from the bed, Isaac leaned down over Jackson who wrapped his arms and legs around him. Isaac picked him up without an issue and carried him over to the couch, laying him down gently. Stiles took the condom off his own dick and threw it in the nearby trash can. 

Then he brought the condom container over and set it down on the floor by the couch, along with the slim bottle of lubrication. The box was new and so far they had blown through two condom packets. Isaac reached forward and grabbed one out, picking up the lube as well. He lightly ripped it open and took out the beige condom, placing it on the head of his cock and rolling it down. After lubing up, he slipped back inside Jackson. 

Jackson gazed up at him with an open mouth. He felt himself falling in lust with the sensation of Isaac’s cock up his ass. The same thing was also happening with Stiles’ amazing dick as well. 

“I’m gonna fuck this bubble butt all night long,” Isaac declared. 

Stiles decided to surprise Jackson. He stood up and dragged his ballsack across Jacksons face. Jackson nuzzled up into Stiles’ balls and loved the way they felt lying everywhere on his face. Then after Stiles moved off for a second, Isaac leaned down momentarily and thrusted on top of Jackson, lightly sweating from all his hard work. 

“That’s it baby, keep sweating on me. Show me how much of a man you are,” Jackson cooed at Isaac. 

In response, Isaac felt his cock harden more and he thrusted powerfully and repeatedly, becoming lost in the absolute haze of pleasure that could not be repeated from anyone else but Jackson. Below, Jackson emitted moan after moan from the cock sliding in and out of his ass. 

“Stiles, let me give your backside some loving,” Jackson said to him.

Stiles grinned and climbed over Jackson, settling down on his legs but hovering at first.

“Tell me what you want,” Stiles said, and then wiggled his ass only a couple inches away from Jacksons face, teasing him. Jackson stared in wonder at the two globes above him. 

“Fuck, I want to caress and nibble on your cheeks, and I want to taste the inside of your asshole, I want it so bad,” Jackson moaned sweetly. 

“Do it in that order then,” Stiles said.

He dropped his ass a little further. Jackson graciously caressed Stiles’ bubble butt and then pecked at it with a hungry mouth. After, he kissed each curved cheek and rubbed against them. He then sat down, and Jacksons face was engulfed by Stiles’ ass. As with Isaac, Jackson loved that there was no option but to breathe in Stiles’ ass while he devoured his hole. 

Jackson licked rapidly across the expanse of Stiles’ puckered entrance. Then his tongue breached through and savored every inch inside Stiles’ asshole. 

“Fuck Jackson, stretch that tongue, get it all the way in there!” Stiles exclaimed. 

As Jackson made love to Stiles’ ass, Stiles and Isaac leaned forward to each other, then kissed deeply. Isaac reached out and slapped Stiles’ pec, holding on with a firm grip which made Stiles groan. All three of them knew what was coming soon. 

Stiles removed himself from Jacksons face. Ready to go full force, Isaac swept up Jackson and carried him back to the bed, then lay him down. Isaac snapped his hips, sliding continuously inside Jackson while he latched onto his own cock and jerked off, feeling it coming close, Stiles jerking off as well. 

And then Jackson let go. He gasped as his orgasm hit in its pure blissful force. Riding it out completely, he dropped his head back and lost himself in a beautiful haze. Stiles continued tugging himself by Jacksons head and Isaac had not lost the speed in his rhythm. Both of them were close and…

Stiles instantly moved closer and then his cum shot out to Jacksons open mouth. He groaned and closed his eyes, letting himself feel his orgasm. Jackson was able to catch most of Stiles’ cum, but a few drops hit part of his face. 

Isaac pounded Jackson at a furious pace, until he pulled out, yanked the condom off, then moved forward and pumped himself hurriedly by Jackson until he felt his ejaculation hit. Isaac breathed heavily with an open mouth and felt such an extent of pleasure and bliss that it truly shocked him. Jackson was also able to catch most of Isaac’s cum. 

All three men were breathing with open mouths and reveling in their pleasure. Stiles let himself lay down on the bed on the right side while Jackson gently moved closer to him. He spoke to Isaac. 

“Isaac, baby, get me a couple of tissues, will you?” Jackson asked sweetly to him.

“Hell, I’d do anything for you at this point,” Isaac said, completely truthful. 

Still eager to please, Isaac got up from the bed and went quickly towards the bathroom. Jackson watched Isaac’s big butt cheeks bounce firmly as he hurried forward, disappearing past the doorframe. Isaac looked around, standing nude inside Jacksons perfectly well-maintained bathroom, then found a tissue box and grabbed a couple of sheets, walking back to the bedroom. 

Jackson cleaned up the remaining cum on his face and some from his stomach. Then he got off the bed and walked to his bathroom where he finished cleaning up. Once that was done, he eagerly slipped back into his bed between Isaac and Stiles. They rested up for the next thirty minutes. Then Jackson got up. 

“I just need to lock up the house,” Jackson said.

He removed himself from the bed and went to the front where his clothes were. Dipping down gently—and while Stiles and Isaac stared at his bare backside—Jackson picked up his underwear and put them back on, followed by his shirt. He exited the bedroom. 

Isaac and Stiles remained in Jacksons bed. Their strong chests heaved up and down while their lower halves were covered by the sheets. 

“You were fucking great, man,” Isaac said, grinning and punching Stiles’ arm.

“Dude, you were a fucking stud,” Stiles said, just as excited. 

Downstairs, Jackson locked up for the night. The main doors had already been secured, but he checked them again nonetheless. After setting the alarm, he went up the stairs and followed the hall down to his bedroom.

Jackson slipped out of his clothes again, then slotted himself between the two Lacrosse players. 

Stiles was the last to fall asleep, but his eyelids immediately started weakening, until they closed and he couldn’t even realize he had fallen asleep. 

It had been a night none of them would ever forget.


End file.
